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The Venture Codex

Matchstick Ventures

1380 Raymond Jessup Rd, Mount Airy, North Carolina, United States

Overview

Matchstick Ventures supports the creation and growth of early-stage technology companies in rapidly growing yet underserved startup ecosystems. The firm prefers to invest in seed-stage, early-stage, and later-stage companies. The firm seeks to invest in the business products, business services, information technology, and TMT sectors.

Total investments
57
Lead investments
11
Investments · 12mo
5
Active investors
5

Sector focus

  • Business Development
  • Financial Services
  • Venture Capital
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Investment portfolio

  • Saile

    Led · Seed · May 2026

    Saile combines a portable credential passport for physicians with a shift marketplace and five modular AI agents that automate recruiting, onboarding, credentialing, staffing, and compliance. The platform stores and tracks doctors’ licenses, certifications, and documents, issues alerts before expirations, and claims to shorten onboarding timelines by roughly 45 days while cutting administrative work for facilities by about 40%. Founded out of work that began in early 2025 by neurosurgeon Marc Ayoub and Taylor Hakes, the company has grown to nearly 5,000 active physician users and operates with a core team of four. Its primary revenue approach is a per-seat SaaS model for facilities, alongside three other revenue streams. Saile intends to use its $2.2M pre-seed funding to expand AI agent infrastructure, enhance marketplace capabilities, and deepen integrations with facility credentialing systems.

  • Two Boxes

    Participated · Equity · Apr 2026

    Two Boxes offers an AI-driven returns processing platform that uses image classification, anomaly detection, and fraud identification to modernize reverse logistics for retailers, direct-to-consumer brands, and logistics providers. The platform enables faster inventory recovery, reduced fraud-related losses, and improved operational efficiency, and currently processes nearly $1 billion in returned inventory value annually across three continents. Two Boxes has shown rapid 2025 growth, onboarding about two third-party logistics providers per month and one new merchant per day, and serves enterprise clients including Stord, Cart.com, and Radial. The company positions itself as foundational returns infrastructure amid rising returns volumes and returns-related fraud in e-commerce. With the new capital, Two Boxes plans to accelerate product development, expand enterprise adoption, and grow its presence beyond North America. No revenue or valuation figures were disclosed in the articles.

  • Great Sky

    Participated · Seed · Mar 2026

    Great Sky builds a computing architecture that integrates superconducting computation, high-bandwidth optical connectivity, and semiconductor circuitry to enable brain-like, low-latency, energy-efficient AI processing. The team traces its work to 12 years of research at the U.S. National Institute of Standards and Technology, producing 23 peer-reviewed publications and eight patents. Its first-generation chips have completed tape-outs and the company reports integration of components into complete neural networks, with claimed performance such as processing over 60 million video frames per second in video-analysis scenarios. Great Sky plans to manufacture its technology in scalable processes and pursue multi-modular cognitive systems by tiling wafer-scale networks with advanced fiber-optic interconnection. Financially, the company disclosed a $14 million seed round led by Bison Ventures to support these development and commercialization efforts. The company was founded by CEO Jeff Shainline, CTO Jeff Chiles, VP of Fabrication Saeed Khan, and VP of Architecture Bryce Primavera.

  • Mentium

    Participated · Seed · Oct 2025

    Founded in 2023 and headquartered in Austin, Texas, Mentium is an AI-native platform that lets freight brokerages and logistics providers deploy task-specific “digital workers.” The company’s agents plug into TMS, ERP, email, phone, SMS, and third-party chat apps to create a single source of truth and automate repetitive processes without coding or pre-training. Its initial product tackles accounts-payable automation for carrier payments—a labor-intensive, revenue-leaking workflow—while additional agents handle load booking, rate negotiation, reporting, and customer–carrier communications. Early customers such as Baker Tilly (Panama), Sethmar, Heartland Logistics Group, and Continental Expedited Services report up to 70 % of tasks completed with zero human touch. Mentium positions itself as the future “operating system for logistics,” aiming to expand automation across an enterprise once integrated. Strategic partnerships with Google, AWS, and NVIDIA support enterprise-grade scalability and compliance. Proceeds from the latest funding will accelerate product development, broaden go-to-market efforts, and grow the engineering team.

  • Pageport

    Led · Equity · Aug 2025

    Pageport builds technology to help financial advisors grow their practices and strengthen client relationships. The company is trusted by more than 1,000 advisors and offers marketing and client engagement tools. Pageport launched Slant, an AI-first CRM designed exclusively for financial advisors that automates meeting preparation, follow-ups, scheduling, compliance workflows, and personalized outreach. Slant uses AI agents—nudges, meeting & scheduling agents, and an embedded chat assistant—to draft outreach, prepare agendas and documents, manage scheduling, log notes, and queue follow-ups. Pageport says Slant is built to double advisor capacity so advisors can serve hundreds more clients and help close the financial advice gap. The company plans a nationwide rollout supported by a $3.3 million funding round announced Aug. 26, 2025. Pageport offers “websites for one”: a platform that lets users create personalized pages tied to a unique URL and vertical video for each lead. The product supports templates for different funnels, in-app video creation, galleries and other sections, and eight CRM integrations to populate prospect attributes. Pageport automatically sends a unique, personalized URL to leads so each recipient sees tailored content. Early use cases include financial advisors, photographers and early-stage SaaS companies that generate high lead volumes. In five months of full-time operation the founders brought on over 70 customers, created more than 250,000 custom websites, and exceeded six-figures of ARR via founder-led sales. Founders Thomas Clawson and Max Metcalf built an MVP in February 2023, validated in March, and quit their jobs in May 2023 to focus on the company.

Team